Salts of sulfated fatty amine glycosides



SALTS or SULFATED FATTY AMINE GLYCOSIDES John G. Erickson, Minneapolis, Minn., assignor to General Mills, Inc., a corporation of Delaware No Drawing. Application August 3, 1953 Serial No. 372,143

7 Claims. (Cl. 260-211 The present invention relates to water-soluble salts of sulfated fatty amine glycosides. These compounds are novel emulsifying agents and fabric softeners.

. 'It is, therefore, an object of the present invention to provide novel compounds having the above composition.

The invention is applicable to any reducing sugar capable of forming the fatty amine glycosides. These may be monosaccharides including the pentoses and hexoses whether aldose or ketose, and also the disaccharides having a reducing carbonyl group. Suitable sugars include glucose, lactose, maltose, gentiobiose, cellobiose, melibiose, mannose, ribose, xylose, galactose, lyxose, gulose and allose.

The fatty amines which may be employed for formation of the glycosides are the primary fatty amines containing from 8-22 carbon atoms and being derived from fatty acids. The amines may be single isolated amines or may be the mixed amines derived from the mixed fatty acids of a fat or oil or from any selected fraction thereof. The amines may be either saturated or unsaturated.

The glycosides' may be made as disclosed in my copending application, Serial No. 261,385, filed December 12, 1951, now abandoned. According to this application the reaction between thesugar and the fatty amine may be carried out in the presence of a lower aliphatic alcohol at temperatures of from 1540 C. The reaction between aldoses and fatty amines proceeds readily to form the glycoside. With ketoses there is a tendency for the glycoside to react with further fatty amines to introduce another fatty amino group into the glycoside molecule. Accordingly, with the ketoses it is preferred to use quite a large excess of the sugar over the amine to obtain a satisfactory yield of the glycoside.

These glycosides may then be sulfated by means of any conventional sulfating agent such as chlorosulfonic acid, sulfur trioxide or sulfuric acid. The number of sulfate groups introduced into the molecule will vary depending upon the product desired. In general, from 1-4 sulfate groups are introduced into the glycosides. Where the fatty amine group contains a long chain group such as the C to C group, it is usually preferable to introduce 2-4 sulfate groups in order to produce a product which will have detergent properties. On the other hand, where it is desired to produce a textile softener, it is not essential that the product have the same balance of hydrophilic and lipophilic character and a lesser number of sulfate groups will suflice. Similarly, where a shorter chain amine is employed, for example one containing from 8-14 carbon atoms, from 1-2 sulfate groups will be sufficient to produce a detergent or emulsifying agent. Therefore, depending upon the particular sugar employed, the characteristics of the fatty amino group and the use to which the resultant product is to be put, the number of sulfate groups may be varied accordingly. The number of sulfate groups introduced can be controlled simply by controlling the amount of the sulfating agent used.

The sulfation reaction is preferably carried out at temperatures of from 50 C., at which temperature ate Q Ti thereaction proceeds very readily. Chloroform is a very satisfactory solvent for the reaction, although other inert solvents such as carbon tetrachloride or tetrachloroethane may be used. After the reaction is completed the. sulfate I groups maybe neutralized with alkalime tal hydroxides or carbonates such as sodium or. potassium hydroxide or carbonate, or by means of ammonium hydroxide. The neutralization reaction may be carried out by adding aqueous or alcoholic solutions of the alkaline material to the sulfation mixture. The solid products may be obtained by evaporation of the neutralization mixture.

Example 1 To a suspension of 0.69 part of dodecylamine glucoside in 37 parts'of chloroform was added dropwise 0.23 part of chlorosulfonic acid at 25 C. An aqueous-alcoholic Example 2 A solution of 9.28 parts of chlorosulfonic acid in 37 parts of chloroform was added dropwise to a suspension of 8.62 parts of octadecylamine glucoside in 148 parts of chloroform at 25 C. The mixture was then made slightly alkaline with aqueous-alcoholic sodium hydroxide and then made faintly acidic with acetic acid. Evaporation of the mixture left a greenish-brown solid, the tetrasodium salt of the tetrasulfate of octadecylamine glucoside. Solutions of this material in water foamed.

Example 3 To a suspension of 5.2 parts of dodecylamine maltoside in 150 parts of chloroform was added dropwise a solution of 1.2 parts of chlorosulfonic acid in 15 parts of chloroform. The solid dissolved rapidly. The mixture was made slightly basic with aqueous methanolic sodium hydroxide, then slightly acidic with acetic acid. Filtration, followed by evaporation, yielded the sodium salt of the monosulfate of dodecylamine maltoside as a light brown solid. It showed excellent emulsifying power for dispersing hydrocarbons in water. Cloth soaked in an aqueous solution of this material, then dried, was

noticeably softer to the touch than untreated cloth.

Example 4 I To a suspension of 5.9 parts of octadecylamine lactoside in 150 parts of chloroform was added dropwise 3.5 parts of chlorosulfonic acid. The solid all dissolved. The mixture was made somewhat basic with aqueous sodium hydroxide solution, then faintly acidic with acetic acid. Evaporation of the mixture left the trisodium salt of the trisulfate of octadecylamine lactoside. This dissolved in water to give a solution which foamed well.

I claim as my invention:

1. An alkali metal salt of a sulfated fatty amine N-glycoside, the fatty amine group containing from 8-22 carbon atoms.

2. The sodium salt of a sulfated fatty amine N-glysoside, the fatty amine group containing from 8-22 carbon atoms.

3. An alkali metal salt of a sulfated fatty amine N-glycoside, the fatty amine group containing from Patented June 10, 1958 of non-surface-active material and- 2,838,487 I y 3 I 4 8-22 carbon atoms and the glycoside containing from References Cited in the file of this patent 1-4 sulfate groups.

4. The sodium salt of the monosulfate of dodecylamine UNITED STATES PATENTS N-glycoside. 2,508,433 Snyder May 23, 1950 5. The 'tetrasodium-salt of the tetrasulfate-of bcta 5 2,689,244 OIIES Sept. 14, 1954 decylamine 'N-glycoside'.

6; The-sodium salt ofthe monosulfate' of dodecyl= FOREIGN PATENTS amine N-maltosidez- 111,256 Australia Aug. 12, 1940 7. The trisodium sa1t of the trisulfate-of octadecyk amine 'N-lactoside; 10 

1. AN ALKALI METAL SALT OF A SULFATED FATTY AMINE N-GYCOSIDE, THE FATTY AMINE GROUP CONTAINING FROM 8-22 CARBON ATOMS. 